Quinoline → (1R,cis)2,2-dimethyl-3-[(Z)3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylic acid

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Reaction Steps

500 mg of 10% palladium hydroxide on barium sulfate and 5 ml of ethyl acetate were placed in a round flask connected to a hydrogen apparatus and 2 g of the product of Step C, 45 ml of ethyl acetate and 0.5 ml of quinoline were added thereto. Hydrogenation was carried out until hydrogen absorption ceased and the mixture was filtered. The filtrate was washed with N hydrochloric acid, then with water and evaporated to dryness. The 2 g of residue were chromatographed over silica gel and eluted with a 70-20-1 cyclohexane-ethyl acetate-acetic acid mixture to obtain 1.3 g of (1R,cis) 2,2-dimethyl-3-[(Z )-3-oxo-3-(2,2,2-trifluoro-ethoxy)-1-propenyl]cyclopropane-carboxylic acid.

Provenance & Evidence